Hydrochloric Acid → 4,4'-Didocosoxybenzhydrol

HRID 573970Notes

Reaction equation

HRID 573970 reaction equation
[CH2:1]([O:23][C:24]1[CH:60]=[CH:59][C:27]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[CH:32][CH:31]=2)=[O:29])=[CH:26][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1COCC1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH:28]([OH:29])[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[CH:32][CH:31]=2)=[CH:59][CH:60]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 667175264,4'-Didocosyloxy-benzophenone

Product 1

HCID 469361424,4'-DidocosoxybenzhydrolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 4,4′-didocosyloxy-benzophenone (28.3 g, 34.1 mmol) were added THF (300 mL) and methanol (15 mL), and the mixture was heated to 60° C. Sodium borohydride (6.10 g, 161 mmol) was slowly added, and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was ice-cooled, and 1N hydrochloric acid (80 mL) was added dropwise. THF was evaporated, water (450 mL) was added, and 1N hydrochloric acid was added to adjust the pH to 5-7. The slurry was filtered, and the obtained crystals were washed with water and methanol to give the title compound (28.5 g, 34.1 mmol, 99%).

Workup

  1. temperaturecooled
  2. customTHF was evaporated
  3. additionwater (450 mL) was added
  4. addition1N hydrochloric acid was added
  5. filtrationThe slurry was filtered
  6. washthe obtained crystals were washed with water and methanol

Sources & evidence

ORD record
ord-25552fb4a7b943029881f2ee7aa5033f
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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