Hydrochloric Acid → HCID 11244477, compound

HRID 860539Notes

Reaction equation

HRID 860539 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:21]4[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17]COC)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl>C1COCC1.C(O)(C)C.O>[C:1]12([C:11]3[CH:12]=[C:13]([C:21]4[CH:22]=[CH:23][C:24]([CH:25]=[O:26])=[CH:27][CH:28]=4)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 2

HCID 313Hydrochloric Acid3×HCID 86586034HCID 86586034, compound

Product 1

HCID 11244477HCID 11244477, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To a solution of 4-[3-(1-adamantyl)-4-methoxymethoxyphenyl]benzaldehyde (6.88 g, 18.30 mmol) in 200 mL of THF:isopropanol (1:1) was a added 30 mL of6 N HCl at room temperature. After 20 hours 30 mL of 12 N HCl was added. After 57 hours starting material was still present, 60 mL of additional 12 N HCl was added and stirred for 16 hours. The resulting mixture was diluted with water and extracted with ether (2×200 mL). The combined organics were washed with water (150 mL), brine (100 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to give 6.00 g (99%) of 4-[3-(1-adamantyl)-4-hydroxyphenyl]benzaldehyde as a solid. 1H NMR (300 MHz; DMSO-d6): δ 1.72 (brs, 6H), 2.00–2.20 (m, 9H), 6.88 (d, J=8.7 Hz, 1H), 7.36–7.48 (m, 2H), 7.78 (d, J=8.1 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 9.67 (s, 1H), 9.98 (s, 1H).

Workup

  1. customat room temperature
  2. extractionextracted with ether (2×200 mL)
  3. washThe combined organics were washed with water (150 mL), brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-53a959f9cef14876bc3ad20b68ad6c52
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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