Hydrochloric Acid → 4-Tetradecyloxybenzyl alcohol

HRID 979548

Reaction equation

HRID 979548 reaction equation
[BH4-].[Na+].[Br-].[Li+].C[O:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:10][CH:9]=1.Cl>COCCOCCOC>[CH2:15]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][OH:6])=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82050Lithium BromideHCID 3312490Methyl 4-(tetradecyloxy)benzoateHCID 4311764Sodium borohydride

Product 1

HCID 100873844-Tetradecyloxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

1.35 g (36 mMols) of sodium borohydride and then 3.1 g (36 mMols) of lithium bromide were stirred into 60 ml of diethylene glycol dimethyl ether. After stirring for 30 minutes, 20.0 g (57 mMols) of 4-tetradecyloxy-benzoic acid methyl ester were added. The mixture was heated for 3.5 hours to 100° C. and poured in portions onto a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid, after which the deposit formed was filtered off and stirred with a little methylene chloride. The undissolved fraction was then filtered off and recrystallized from n-hexane. 4-tetradecyloxybenzyl alcohol melting at 73° to 75° C. was obtained in a yield of 12.5 g.

Workup

  1. temperatureThe mixture was heated for 3.5 hours to 100° C.
  2. customafter which the deposit formed
  3. filtrationwas filtered off
  4. stirringstirred with a little methylene chloride
  5. filtrationThe undissolved fraction was then filtered off
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-69638bbed41146dc98a10cce8ebdda8e
Source dataset
uspto-grants-1987_05
Patent number
US04668705

Linked notes

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