Water → Triphenylcarbinol

HRID 2256818Notes

Reaction equation

HRID 2256818 reaction equation
C(OCC(C[O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)CCOC(=O)C)(=O)C.O>C(O)(=O)C>[C:15]([OH:14])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 962WaterHCID 54490045HCID 54490045, compound

Product 1

HCID 6457TriphenylcarbinolYield 74.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

2-Trityloxymethyl-1,4-butanediol diacetate (60.90 g, 0.136 mol) was dissolved in acetic acid (320 ml) at 100° C. and water, (80 ml) was added. The solution was kept at 100° C. for 15 min, evaporated in vacuum to small volume and cooled to 0° C. The precipitate was filtered off and washed with cold ethyl acetate to give 26.44 g (theory 35.51 g) of tritylalcohol. The combined filtrate was evaporated to small volume. The compound was purified on a silica gel column (500 g SiO2); eluent 0-2700 ml ethyl acetate+n-hexane (1+1), 2700-3740 ml ethyl acetate+n-hexane (2+1), then neat ethyl acetate. The fractions 2540-4800 ml were evaporated to give 14.20 g (51%) of pure 4-acetoxy-2-hydroxy-methylbutyl acetate. TLC on silica (ethyl acetate+n-hexane 1+1): Rf 0.30.

Workup

  1. customevaporated in vacuum to small volume
  2. filtrationThe precipitate was filtered off
  3. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-b43db3b882fd4a6b8c707b5d5ad99aa3
Source dataset
uspto-grants-1997_08
Patent number
US05656617

Reaction notes

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